Ask Amy: Man torn by gigilo role should find new job

October 29, 2013 

Dear Amy: Six months ago I met a beautiful woman who is quite wealthy. We hit it off immediately and began a wild sexual relationship.

I go to her huge home every day and spend the day in bed with her, as I lost my job last year and can't seem to find another one.

She gives me hundreds of dollars in cash every week (which she calls "pocket change"), and I'm saving lots of money for my retirement. The problem is I'm feeling guilty about the whole situation, and I'm starting to feel like I'm being used.

She insists that she loves me. Should I end this relationship while I still have a little pride or should I keep taking her money for my move to Florida?

— Confused

Dear Confused: Why is this woman giving you so much money? Is it because you won't see her unless she pays you? Does she need to have power and control over you? Or is it because she loves you and is being generous?

If you don't like being a gigolo, then stop acting like one. Before accepting the next weekly wad of cash, you should ask her what her motivation is.

If you are in a relationship with someone who loves you (and you don't love her), and this doesn't feel right, perhaps you should return the money, reclaim your pride and find another way to get yourself to Florida.

If you are spending every day in bed with her, this would seriously impede your job search.

Dear Amy: After a decade of trying to no avail to get my husband to participate in our marriage, I've decided to call it quits. The problem is that I am the breadwinner, and it would ruin us financially to split up.

My husband and I are mostly friends but haven't shared an intimate relationship on any level for 10 years. I stopped wearing my wedding ring and moved to another bedroom a few months ago.

How do I explain this change in our relationship to friends and family? I am at peace with this decision and, in fact, am feeling unstuck and hopeful for the future for the first time in many years.

— Looking ahead

Dear Looking Ahead: Your friends and family (and your daughter) have probably noticed that you have stopped wearing your wedding ring. This gives you an opportunity to say that you and your husband are separating but have decided to continue to cohabit peacefully and co-parent your daughter.


You can contact Amy Dickinson via email at, follow her on Twitter @askingamy or "like" her on Facebook.

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